How does KAYAK find such low prices on flights from Hawaii to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hawaii to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Hawaii to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hawaii with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$212 CHEAP FLIGHTS from Hawaii to Chicago

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Cheap Flights from Hawaii to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Hawaii to Chicago

Mon, Feb 22 - Tue, Mar 2

12:45 pm - 1:54 pmLIH Lihue-ORD Chicago O'Hare Intl

21h 09m1 stop San Diego

2:54 pm - 4:09 pmORD Chicago O'Hare Intl-LIH Lihue

29h 15m1 stop San Diego

$424Alaska Airlines

Mon, Feb 22 - Tue, Mar 2

5:11 pm - 1:54 pmLIH Lihue-ORD Chicago O'Hare Intl

16h 43m2 stops Honolulu San Diego

7:55 pm - 4:09 pmORD Chicago O'Hare Intl-LIH Lihue

24h 14m1 stop San Diego

$429Multiple Airlines

Mon, Feb 22 - Tue, Mar 2

5:59 pm - 1:54 pmLIH Lihue-ORD Chicago O'Hare Intl

15h 55m2 stops Honolulu San Diego

7:55 pm - 4:09 pmORD Chicago O'Hare Intl-LIH Lihue

24h 14m1 stop San Diego

$429Multiple Airlines

Thu, Oct 22 - Mon, Oct 26

9:53 pm - 1:30 pmLIH Lihue-ORD Chicago O'Hare Intl

10h 37m1 stop Seattle/Tacoma Intl

7:35 am - 7:14 pmORD Chicago O'Hare Intl-LIH Lihue

16h 39m2 stops Salt Lake City Seattle/Tacoma Intl

$430Delta

Thu, Oct 22 - Mon, Oct 26

9:53 pm - 6:10 pmLIH Lihue-ORD Chicago O'Hare Intl

15h 17m2 stops Seattle/Tacoma Intl Salt Lake City

7:35 am - 7:14 pmORD Chicago O'Hare Intl-LIH Lihue

16h 39m2 stops Salt Lake City Seattle/Tacoma Intl

$435Delta

Mon, Nov 2 - Mon, Nov 9

11:09 pm - 6:59 pmHNL Honolulu-ORD Chicago O'Hare Intl

15h 50m1 stop San Diego

7:20 am - 3:21 pmORD Chicago O'Hare Intl-HNL Honolulu

12h 01m1 stop San Diego

$498Alaska Airlines

Mon, Nov 9 - Mon, Nov 16

8:15 am - 5:00 amHNL Honolulu-MDW Chicago Midway

16h 45m1 stop San Jose

10:05 am - 7:30 pmMDW Chicago Midway-HNL Honolulu

13h 25m1 stop Los Angeles

$506Southwest

Mon, Nov 2 - Mon, Nov 9

10:50 pm - 5:15 pmHNL Honolulu-MDW Chicago Midway

14h 25m1 stop San Jose

7:30 am - 9:10 pmMDW Chicago Midway-HNL Honolulu

17h 40m2 stops Baltimore/Washington San Jose

$512Southwest

Mon, Nov 2 - Mon, Nov 9

7:00 pm - 7:27 amHNL Honolulu-ORD Chicago O'Hare Intl

8h 27mnonstop

10:00 am - 3:18 pmORD Chicago O'Hare Intl-HNL Honolulu

9h 18mnonstop

$564American Airlines

Wed, Dec 2 - Mon, Dec 7

7:00 pm - 7:20 amHNL Honolulu-ORD Chicago O'Hare Intl

8h 20mnonstop

11:10 am - 4:48 pmORD Chicago O'Hare Intl-HNL Honolulu

9h 38mnonstop

$567American Airlines

Recent last minute flight deals from Hawaii to Chicago

Thu, Oct 8 - Fri, Oct 9

1:05 pm - 5:15 amLIH Lihue-ORD Chicago O'Hare Intl

11h 10m1 stop Los Angeles

12:40 pm - 7:44 pmORD Chicago O'Hare Intl-LIH Lihue

12h 04m1 stop San Francisco

$494United Airlines

Tue, Oct 13 - Sun, Oct 18

10:40 pm - 4:53 pmHNL Honolulu-ORD Chicago O'Hare Intl

13h 13m1 stop Seattle/Tacoma Intl

5:27 am - 1:36 pmORD Chicago O'Hare Intl-HNL Honolulu

13h 09m1 stop Atlanta Hartsfield-Jackson

$670Delta

Thu, Oct 8 - Fri, Oct 9

1:05 pm - 4:45 amLIH Lihue-ORD Chicago O'Hare Intl

10h 40m1 stop Los Angeles

8:50 am - 7:44 pmORD Chicago O'Hare Intl-LIH Lihue

15h 54m2 stops Los Angeles San Francisco

$670United Airlines

Sun, Oct 11 - Thu, Oct 15

3:30 pm - 8:39 amHNL Honolulu-ORD Chicago O'Hare Intl

12h 09m1 stop Atlanta Hartsfield-Jackson

12:50 pm - 7:48 pmORD Chicago O'Hare Intl-HNL Honolulu

11h 58m1 stop Seattle/Tacoma Intl

$670Delta

Fri, Oct 9 - Mon, Oct 12

12:05 pm - 5:40 amHNL Honolulu-MDW Chicago Midway

12h 35m1 stop Ontario

10:55 pm - 11:50 amMDW Chicago Midway-HNL Honolulu

17h 55m1 stop Las Vegas Harry Reid Intl

$813Southwest

Fri, Oct 9 - Mon, Oct 12

8:55 pm - 8:40 pmHNL Honolulu-MDW Chicago Midway

18h 45m2 stops Phoenix Sky Harbor Intl Dallas Love Field

10:55 pm - 11:50 amMDW Chicago Midway-HNL Honolulu

17h 55m1 stop Las Vegas Harry Reid Intl

$896Southwest

Fri, Oct 9 - Mon, Oct 12

8:40 pm - 1:52 pmHNL Honolulu-ORD Chicago O'Hare Intl

12h 12m1 stop Los Angeles

6:00 am - 12:36 pmORD Chicago O'Hare Intl-HNL Honolulu

11h 36m1 stop Los Angeles

$905American Airlines

Fri, Oct 9 - Mon, Oct 12

12:10 pm - 1:25 pmHNL Honolulu-ORD Chicago O'Hare Intl

20h 15m1 stop San Diego

6:00 am - 4:57 pmORD Chicago O'Hare Intl-HNL Honolulu

15h 57m2 stops Seattle/Tacoma Intl Lihue

$1,003Multiple Airlines

Thu, Oct 8 - Sat, Oct 10

11:30 pm - 8:11 pmHNL Honolulu-ORD Chicago O'Hare Intl

15h 41m2 stops Seattle/Tacoma Intl Boise Air Term. Gowen Fld

8:09 am - 10:18 pmORD Chicago O'Hare Intl-HNL Honolulu

19h 09m2 stops Santa Ana J. Wayne/Orange Cnty San Francisco

$1,257Multiple Airlines

Wed, Oct 7 - Tue, Oct 13

3:33 pm - 12:21 pmKOA Kona Intl-ORD Chicago O'Hare Intl

15h 48m1 stop Los Angeles

5:00 am - 2:03 pmORD Chicago O'Hare Intl-KOA Kona Intl

14h 03m1 stop Phoenix Sky Harbor Intl

$2,583American Airlines

Useful Info

Low season	January
High season	November

Best time to beat the crowds with an average 32% drop in price.

Most popular time to fly with an average 6% increase in price.

How does KAYAK find such low prices on flights from Hawaii to Chicago?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hawaii to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Hawaii to Chicago?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hawaii with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Chicago?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Merrillville

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Chesterton

Schererville

Munster

Porter

Monticello

Saint John

Griffith

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$212 Find Cheap Flights from Hawaii to Chicago - Compare and Save

Cheap Flights from Hawaii to Chicago

Recent round-trip flight deals from Hawaii to Chicago

Recent one-way flight deals from Hawaii to Chicago

Recent last minute flight deals from Hawaii to Chicago

Recent direct flight deals from Hawaii to Chicago

Good to know

Low season

High season

FAQs for booking flights from Hawaii to Chicago

Traveling to a place near Chicago?

More options for your flight to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Cabin class types available on flights to Hawaii

Find direct flights for Chicago

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Flights to other popular destinations

Find deals for your return flight